1-Bromo-3-chloropropane → 1-(3-Chloropropyl)indolin-2-one

HRID 911718Notes

Reaction equation

HRID 911718 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].Br[CH2:12][CH2:13][CH2:14][Cl:15].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:15][CH2:14][CH2:13][CH2:12][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 321710Oxindole

Product 1

HCID 180699061-(3-Chloropropyl)indolin-2-oneYield 39.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Reflux together oxindole (2.66 g, 20.0 mmol), 1-bromo-3-chloropropane (2.56 mL, 26.0 mmol) and potassium carbonate (5.52 g, 40.0 mmol) in acetonitrile (300 mL) under nitrogen for 16 h. Cool the suspension to room temperature and filter off the precipitate. Concentrate the filtrate in vacuo and purify the crude mixture by chromatography on silica gel eluting with isohexane/EtOAc (1:0 to 3:2 gradient over 40 min) to give the title compound as an orange oil (1.65 g, 39%). MS (ES+) m/z: 210 (M+H)+.

Workup

  1. filtrationfilter off the precipitate
  2. concentrationConcentrate the filtrate in vacuo
  3. custompurify the crude mixture by chromatography on silica gel eluting with isohexane/EtOAc (1:0 to 3:2 gradient over 40 min)

Sources & evidence

ORD record
ord-3de14430f73942abbb0af95598742218
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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